GB1007333A - Organosilicon compounds containing phosphorus - Google Patents
Organosilicon compounds containing phosphorusInfo
- Publication number
- GB1007333A GB1007333A GB1946261A GB1946261A GB1007333A GB 1007333 A GB1007333 A GB 1007333A GB 1946261 A GB1946261 A GB 1946261A GB 1946261 A GB1946261 A GB 1946261A GB 1007333 A GB1007333 A GB 1007333A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phosphorus
- silanes
- dichlorosilane
- hydrolysis
- siloxanes
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title abstract 6
- 229910052698 phosphorus Inorganic materials 0.000 title abstract 6
- 239000011574 phosphorus Substances 0.000 title abstract 6
- 150000003961 organosilicon compounds Chemical class 0.000 title 1
- -1 hydrocarbon radical Chemical class 0.000 abstract 8
- 229920000642 polymer Polymers 0.000 abstract 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 4
- 150000004756 silanes Chemical class 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- 239000004215 Carbon black (E152) Substances 0.000 abstract 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 3
- 239000005864 Sulphur Substances 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- 229920001577 copolymer Polymers 0.000 abstract 3
- 229930195733 hydrocarbon Natural products 0.000 abstract 3
- 230000007062 hydrolysis Effects 0.000 abstract 3
- 238000006460 hydrolysis reaction Methods 0.000 abstract 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 abstract 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 abstract 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 abstract 2
- 238000007334 copolymerization reaction Methods 0.000 abstract 2
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 abstract 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- 229910000077 silane Inorganic materials 0.000 abstract 2
- RJVOMEJSSMBACE-UHFFFAOYSA-N 2-[dichloro(methyl)silyl]ethyl-diphenylphosphane Chemical compound C[Si](Cl)(Cl)CCP(C1=CC=CC=C1)C1=CC=CC=C1 RJVOMEJSSMBACE-UHFFFAOYSA-N 0.000 abstract 1
- QGXQMHPQYLAOIQ-UHFFFAOYSA-N [dichloro(methyl)silyl]methyl-diphenylphosphane Chemical compound C[Si](Cl)(Cl)CP(C1=CC=CC=C1)C1=CC=CC=C1 QGXQMHPQYLAOIQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- USJRLGNYCQWLPF-UHFFFAOYSA-N chlorophosphane Chemical class ClP USJRLGNYCQWLPF-UHFFFAOYSA-N 0.000 abstract 1
- 239000011248 coating agent Substances 0.000 abstract 1
- 238000000576 coating method Methods 0.000 abstract 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 abstract 1
- 229920001971 elastomer Polymers 0.000 abstract 1
- 239000000806 elastomer Substances 0.000 abstract 1
- 239000012530 fluid Substances 0.000 abstract 1
- 239000011953 free-radical catalyst Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 239000000314 lubricant Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 abstract 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 125000004437 phosphorous atom Chemical group 0.000 abstract 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 abstract 1
- 229920001296 polysiloxane Polymers 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 150000003568 thioethers Chemical group 0.000 abstract 1
- 239000005051 trimethylchlorosilane Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/30—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen phosphorus-containing groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
- C07F9/5304—Acyclic saturated phosphine oxides or thioxides
- C07F9/5308—Acyclic saturated phosphine oxides or thioxides substituted by B, Si, P or a metal
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Silicon Polymers (AREA)
Abstract
The invention comprises silanes of the general formula <FORM:1007333/C3/1> wherein R is a monovalent hydrocarbon radical free from aliphatic unsaturation; Z is the group -R12P where R1 is alkyl or aryl and may contain oxygen or sulphur attached to phosphorus; X is halogen; n is 2 or 3 and x=0, 1 or 2. The silanes may be prepared by (1) Wurtz synthesis using chloroalkyl silanes and chlorophosphines, (2) Arbusor or Michaelio Arbusor reaction and (3) reacting a secondary phosphine R12P-H with a silane containing olefinic unsaturation. The reaction may be carried out at 0 DEG C. to the reflux temperature of the reactants in the presence of a free radical catalyst, e.g. azobisisobutyronitrile. Pentavalent phosphorus atoms are obtained by using secondary phosphine oxides or sulphides or by reaction of tervalent phosphorus containing silane in the presence of HgO or sulphur. Polymers containing pentavalent phosphorus may be obtained by hydrolysis of the corresponding silanes or by treating polymers containing trivalent phosphorus with hydrogen peroxide or sulphur. Hydrolysis of the halosilanes to siloxanes having the general formula <FORM:1007333/C3/2> wherein Z and R are as above and a=0, 1 or 2 is effected by dissolving in benzene or toluene and adding water at 0 DEG to 15 DEG C. Siloxane copolymers may also be prepared containing the unit <FORM:1007333/C3/3> wherein A is a monovalent hydrocarbon or substituted hydrocarbon radical and y=0, 1, 2 or 3 by (a) cohydrolysing the corresponding silanes, e.g. cohydrolysis of dimethyl dichlorosilane, methyl (diphenyl phosphinomethyl) dichlorosilane and trimethyl chlorosilane, or (b) catalystic copolymerization of phosphorus containing siloxanes with siloxanes containing the above unit in presence of KOH, e.g. copolymerization of a phenylmethylpolysiloxane with ethyl (diphenylphosphinoethyl) polysiloxane. The polymers and copolymers may be used as lubricants and in the preparation of elastomers and resinous coating materials. Examples describe the preparation of <FORM:1007333/C3/4> <FORM:1007333/C3/5> <FORM:1007333/C3/6> (4) a viscous fluid polymer of M.W. 2050, by hydrolysis of <FORM:1007333/C3/7> (5) a solid of M.W. 2120 when the starting material in (4) is treated with H2O2; (6) a copolymer of the hydrolysed products of methyl (diphenyl phosphinoethyl) dichlorosilane and dimethyl dichlorosilane; (7) a product containing a > P=O group obtained by action of H2O2 on the product of (6); <FORM:1007333/C3/8> <FORM:1007333/C3/9> (9) the disiloxane prepared in (8) was treated with octamethylcyclotetra siloxane in presence of KOH to form a homogeneous polymer.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1946261A GB1007333A (en) | 1961-05-30 | 1961-05-30 | Organosilicon compounds containing phosphorus |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1946261A GB1007333A (en) | 1961-05-30 | 1961-05-30 | Organosilicon compounds containing phosphorus |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1007333A true GB1007333A (en) | 1965-10-13 |
Family
ID=10129772
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1946261A Expired GB1007333A (en) | 1961-05-30 | 1961-05-30 | Organosilicon compounds containing phosphorus |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1007333A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2189463A1 (en) * | 1972-06-15 | 1974-01-25 | Union Carbide Corp | Polymeric catalyst precursor - comprising complex of a polysilsesquioxane and palladium or platinum |
-
1961
- 1961-05-30 GB GB1946261A patent/GB1007333A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2189463A1 (en) * | 1972-06-15 | 1974-01-25 | Union Carbide Corp | Polymeric catalyst precursor - comprising complex of a polysilsesquioxane and palladium or platinum |
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